Happy September and Labor Day! I hope this day finds you resting and enjoying some family and friend time as we celebrate our workers on this day. Don’t worry – I’ll be quick, so you can take these nuggets back to the family barbeque conversation. I will do the same!

Over three-day holiday weekends, we tend to take a little time to ponder many big decisions that lie ahead of us. Maybe you’ve been pondering one of these:

• Should I take a trip before the year ends?

• What school should I send my child to next year?

• Do I stay at my job, or leave?

• Should I go out and take advantage of a Labor Day sale? (OK, maybe this one isn’t a big decision, but I couldn’t help it)

• Should I get a financial planner?

Many of our decisions have financial implications. So, you can imagine how thrilled I was when I read the New York Times article, “How to Make a Big Decision?” Here’s a snippet that should provide some encouragement for you:

“If you find yourself mapping a “whether or not” question, looking at a simple fork in the road, you’re almost always better off turning it into a “which one” question that gives you more available paths….And yet hard choices require us to make those kinds of imaginative leaps: to discover new paths and outcomes that had not been visible to us when we first started wrestling with the decision. It is the nature of complex decisions that they are all unique constellations of variables.”

Powerful, right? Well, here’s how it relates –

For instance, let's say you are looking for a financial planner, and the first one you meet sounds great. Instead of saying, “Should I go with him or should I not go with him?,” make sure you explore various options. As I’ve talked about before on my video, it’s important to date around (with financial advisors, of course) before you decide on one. In short, make sure you have alternative options because it can be easy to be anchored in a “yes/no” framework, which limits your ability to make the optimal decision for you.

While you’re letting that sink in, I want you to ponder these two questions, which will help you on your wealth journey:

• Are you (or someone you know) starting a business that involves tech, but you’re not a techie? Fear not. Read my recent American Express OPEN article, 3 Product Development Strategies for Non-Techies, which will equip you with the confidence to bring a technological solution to market. You should: (1) Surround yourself with A+ workers, tech advisors and mentors, (2) Create a culture of innovation and testing, and (3) Learn the language of product development

• Want to make a smart investing move? You should always aim to get a higher return on your investments than the rate of debt that you owe. For example, if you can earn 7% in the stock market on $20,000, and you also owe $20,000 at 5% debt, you should take that trade because the interest on your investment is higher. Recently, we saw the City of Chicago, one of the first cities attempt to make this move at a large government level. You see, it’s not all bad in Chicago – It’s personal for me because I live here. According to the Wall Street Journal, Chicago is considering a $10 billion taxable bond offering that would be used to help close Chicago’s $28 billion pension funding gap. Chicago is betting that it can earn more investing the proceeds than it paid to issue the new debt, setting an example for other large governments wrestling with sizable pension deficits. Now, this strategy does not come without risk, but recognize that these types of investment strategies are relevant for you and me because they offer us ways to make smart money choices.

Have something to share on making decisions, starting your new business, or making a smart investment move. Leave a comment below.